MXPA06000162A - SYNTHESIS OF beta-L-2-DEOXY NUCLEOSIDES. - Google Patents

SYNTHESIS OF beta-L-2-DEOXY NUCLEOSIDES.

Info

Publication number
MXPA06000162A
MXPA06000162A MXPA06000162A MXPA06000162A MXPA06000162A MX PA06000162 A MXPA06000162 A MX PA06000162A MX PA06000162 A MXPA06000162 A MX PA06000162A MX PA06000162 A MXPA06000162 A MX PA06000162A MX PA06000162 A MXPA06000162 A MX PA06000162A
Authority
MX
Mexico
Prior art keywords
furanosyl
anhydro
deoxy
beta
synthesis
Prior art date
Application number
MXPA06000162A
Other languages
Spanish (es)
Inventor
Alistair Stewart
Original Assignee
Idenix Cayman Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Idenix Cayman Ltd filed Critical Idenix Cayman Ltd
Publication of MXPA06000162A publication Critical patent/MXPA06000162A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/06—Pyrimidine radicals
    • C07H19/09—Pyrimidine radicals with arabinosyl as the saccharide radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H1/00—Processes for the preparation of sugar derivatives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
    • C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
    • C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
    • C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
    • C07H13/08—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals directly attached to carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/20—Carbocyclic rings
    • C07H15/203—Monocyclic carbocyclic rings other than cyclohexane rings; Bicyclic carbocyclic ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/06—Pyrimidine radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/06—Pyrimidine radicals
    • C07H19/073—Pyrimidine radicals with 2-deoxyribosyl as the saccharide radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H9/00—Compounds containing a hetero ring sharing at least two hetero atoms with a saccharide radical
    • C07H9/02—Compounds containing a hetero ring sharing at least two hetero atoms with a saccharide radical the hetero ring containing only oxygen as ring hetero atoms
    • C07H9/04—Cyclic acetals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H9/00—Compounds containing a hetero ring sharing at least two hetero atoms with a saccharide radical
    • C07H9/06—Compounds containing a hetero ring sharing at least two hetero atoms with a saccharide radical the hetero ring containing nitrogen as ring hetero atoms
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Saccharide Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

An improved process for the preparation of 2'-modified nucleosides and 2'-deoxy-nucleosides, such as, beta-L-2'-deoxy-thymidine (LdT), is provided. In particular, the improved process is directed to the synthesis of a 2'-deoxynucleoside that may utilize different starting materials but that proceeds via a chloro-sugar intermediate or via a 2,2'- anhydro-1-furanosyl-nucleobase intermediate. Where an 2,2'-anhydro-1-furanosyl base intermediate is utilized, a reducing agent, such as Red-Al, and a sequestering agent, such as 15-crown-5 ether, that cause an intramolecular displacement reaction and formation of the desired nucleoside product in good yields are employed. An alternative process of the present invention utilizes a 2,2'-anhydro-1-furanosyl base intermediate without a sequestering agent to afford 2'-deoxynucleosides in good yields. The compounds made according to the present invention may be used as intermediates in the preparation of other nucleoside analogues, or may be used directly as antiviral and/or antineoplastic agents.
MXPA06000162A 2003-06-30 2004-06-30 SYNTHESIS OF beta-L-2-DEOXY NUCLEOSIDES. MXPA06000162A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US48371103P 2003-06-30 2003-06-30
US55861604P 2004-04-01 2004-04-01
PCT/US2004/021281 WO2005003374A2 (en) 2003-06-30 2004-06-30 SYNTHESIS OF β-L-2-DEOXY NUCLEOSIDES

Publications (1)

Publication Number Publication Date
MXPA06000162A true MXPA06000162A (en) 2006-03-21

Family

ID=33567697

Family Applications (1)

Application Number Title Priority Date Filing Date
MXPA06000162A MXPA06000162A (en) 2003-06-30 2004-06-30 SYNTHESIS OF beta-L-2-DEOXY NUCLEOSIDES.

Country Status (12)

Country Link
US (1) US20050059632A1 (en)
EP (2) EP1639121A4 (en)
JP (1) JP2007527396A (en)
KR (1) KR20060035652A (en)
AU (1) AU2004254620A1 (en)
BR (1) BRPI0412031A (en)
CA (1) CA2531412A1 (en)
MX (1) MXPA06000162A (en)
NO (1) NO20060469L (en)
NZ (1) NZ544634A (en)
RU (2) RU2361875C2 (en)
WO (1) WO2005003374A2 (en)

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SG162753A1 (en) * 2005-06-07 2010-07-29 Univ Yale Methods of treating cancer and other conditions or disease states using lfmau and ldt
CN101511375B (en) * 2005-12-02 2012-09-05 耶鲁大学 Methods of treating cancer and other conditions or disease states using l-cytosine nucleoside analogs
WO2007075876A2 (en) * 2005-12-23 2007-07-05 Idenix Pharmaceuticals, Inc. Process for preparing a synthetic intermediate for preparation of branched nucleosides
AU2007224441A1 (en) * 2006-03-15 2007-09-20 Novartis Ag Process for preparing L-nucleic acid derivatives and intermediates thereof
GB2443410B (en) * 2006-10-31 2012-05-16 Cb Fleet Co Inc A process for the preparation of 6-bromo-6-deoxy-2,3-anhydro-D-manno-1,4-lactone
US7964580B2 (en) 2007-03-30 2011-06-21 Pharmasset, Inc. Nucleoside phosphoramidate prodrugs
CN101302239B (en) * 2007-05-11 2011-05-11 上海医药工业研究院 Synthetic method of telbivudine and intermediate thereof
CN101531639B (en) * 2009-04-16 2011-10-26 药源药物化学（上海）有限公司 Method for iodinating 5th position of ferric inorganic salt catalyzed 2-pyrimidone and derivatives thereof
NZ716840A (en) 2013-08-27 2017-06-30 Gilead Pharmasset Llc Combination formulation of two antiviral compounds
CN104744538A (en) * 2013-12-26 2015-07-01 康普药业股份有限公司 Telbivudine preparation method
CA2998646C (en) * 2015-09-23 2021-05-18 Merck Sharp & Dohme Corp. 4'-substituted nucleoside reverse transcriptase inhibitors and preparations thereof
CN105732732B (en) * 2016-04-14 2018-04-06 四川理工学院 A kind of method for preparing 2 deoxidation D ribose
BR112021024039A2 (en) * 2019-07-19 2022-02-08 Bp Corp North America Inc Syntheses of substituted furans

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Also Published As

Publication number Publication date
WO2005003374A3 (en) 2005-09-01
EP2157095A3 (en) 2010-09-08
KR20060035652A (en) 2006-04-26
RU2006102518A (en) 2006-07-27
NO20060469L (en) 2006-03-30
RU2361875C2 (en) 2009-07-20
EP1639121A2 (en) 2006-03-29
NZ544634A (en) 2009-10-30
WO2005003374A2 (en) 2005-01-13
JP2007527396A (en) 2007-09-27
US20050059632A1 (en) 2005-03-17
BRPI0412031A (en) 2006-09-19
AU2004254620A1 (en) 2005-01-13
EP1639121A4 (en) 2008-04-16
EP2157095A2 (en) 2010-02-24
RU2009115775A (en) 2010-10-27
CA2531412A1 (en) 2005-01-13

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